acetal mechanism mistakes
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4 سال پیش
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Students often commit mistakes when drawing the acetal mechanism. Two mistakes are particularly common. Mistake #1, in losing water, students will use an SN2 to kick out the water with an alcohol. There are several problems with this step, but perhaps the biggest is that an alcohol is not a strong nucleophile. This transformation instead has the water leave and then the cation is attacked with the alcohol. Mistake #2, students will perform an intramolecular reaction to move protons from one side of the molecule to another. This transition state would require a four-membered ring, which is unlikely. The reaction instead occurs through two steps, an intermolecule deprotonation followed by an intermolecular protonation.
Students often commit mistakes when drawing the acetal mechanism. Two mistakes are particularly common. Mistake #1, in losing water, students will use an SN2 to kick out the water with an alcohol. There are several problems with this step, but perhaps the biggest is that an alcohol is not a strong nucleophile. This transformation instead has the water leave and then the cation is attacked with the alcohol. Mistake #2, students will perform an intramolecular reaction to move protons from one side of the molecule to another. This transition state would require a four-membered ring, which is unlikely. The reaction instead occurs through two steps, an intermolecule deprotonation followed by an intermolecular protonation.
4 سال پیش
در تاریخ 1398/12/03 منتشر شده
است.
418
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